Hydrochloric Acid → HCID 78321673, compound

HRID 2201931Notes

Reaction equation

HRID 2201931 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl.[NH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>O1CCCC1.C(#N)C>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([NH:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 122755Glycine methyl ester hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 76286162HCID 76286162, compound

Product 1

HCID 78321673HCID 78321673, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-3-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid (40 mg, 0.119 mmol), methyl 2-aminoacetate hydrochloride (19.35 mg, 0.154 mmol), and TEA (0.050 mL, 0.356 mmol) in tetrahydrofuran (1 mL) and acetonitrile (1 mL) was added HATU (54.1 mg, 0.142 mmol). The reaction was stirred at 60° C. for 2 h. The mixture was added 1M HCl and purified by HPLC to give the title compound. LCMS m/z=409.1 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.27 (d, J=6.8 Hz, 0.3H), 1.46 (d, J=6.5 Hz, 2.7H), 1.70-1.82 (m, 1H), 2.01-2.12 (m, 2H), 2.23-2.33 (m, 1H), 2.56 (t, J=7.7 Hz, 2H), 2.96 (t, J=7.8 Hz, 2H), 3.07-3.21 (m, 4H), 3.36-3.47 (m, 1H), 3.49-3.61 (m, 1H), 3.69 (s, 3H), 3.73-3.83 (m, 1H), 3.90 (d, 6.0 Hz, 2H), 6.80 (s, 1H), 7.34 (d, J=8.1 Hz, 2H), 7.38 (d, J=8.1 Hz, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.63 (d, J=8.2 Hz, 2H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-4e3282a47c9d45fd8961f65735fd0739
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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